R. Bruni et al. / Tetrahedron: Asymmetry 17 (2006) 2287–2291
2291
6
[
(
a] = +41 (c 5.1, CHCl ); for (1R,5S,6R)-9 [a] = À68
GLC using biphenyl as the internal standard. The best
results are reported in Table 4.
D
3
D
2
7
c 1.1, CHCl ); for (1R,5S,6S)-10 [a] = À91 (c 2.6,
3
D
2
8
3 D
CHCl ); for (1S,2R)-11 [a] = +18 (c 1.0, MeOH); for
2
9
(
1R,2R)-12 [a] = À38.2 (c 9.6, EtOH).
D
References
4
.2. Reduction of ketones 1–5 with plants (differentiated cells)
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the proper substrate (0.1 g in 1 ml of DMSO) were added.
The suspension was maintained at 25 ꢁC in the dark and
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9.
1
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À4
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2
L) and kinetin (1 · 10 g/L) were added. For Oriza sativa,
2
0
(
1
À4
À3
· 10 g/L), 1-naphthalenacetic acid (NNA, 1 · 10 g/
À3
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À3
À3
2
6, 995.
1
5. Hamada, H.; Nakamura, N.; Ito, S.; Kawabe, S.; Funamoto,
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The plants are washed with demineralized sterile water,
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again with water and then treated with ethanol (20 min).
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of the selected plant (5 mm) obtained with a sterilized cut-
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appropriate agarized medium. After 2 weeks at 25 ꢁC in the
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1
1
6. Hamada, H. Bull. Chem. Soc. Jpn. 1988, 61, 869.
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2
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.4. Reduction of ketones 3 and 5 with plants (undifferenti-
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2
2
The culture medium was prepared by dissolving in demin-
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3
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2
4. Baldassarre, F.; Bertoni, G.; Chiappe, C.; Marioni, F. J. Mol.
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(
Sigma)
(3.69 g/L),
saccharose
(30 g/L),
biotin
À4
(
2
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2
7. Dawson, M. J.; Lawrence, G. C.; Lilley, G.; Todd, M.;
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The culture medium (100 mL), previously sterilized at
1
20 ꢁC for 20 min, was inoculated with the undifferentiated
cells (1 g) of the selected plant (Table 3), and chloramphen-
icol (40 mg) was added. The suspension was stirred
1
983, 2119.
(
120 rpm) for 24 h in the dark at room temperature. A
grown culture was added followed by the proper substrate
100 lL from a solution containing 0.1 g in 1 ml of EtOH).
Aliquots were withdrawn periodically and monitored by
2
8. Matsumoto, K.; Kawabata, Y.; Takahashi, J.; Fujita, Y.;
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(
29. Hirata, T.; Izumi, S.; Akita, K.; Yoshida, H.; Gotoh, S.
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